Potassium Carbonate → [1-[2-[3-(3,4-Dichlorophenyl)-1-(3,4,5-trimethoxybenzoyl)pyrrolidin-3-yl]ethyl]piperidin-4-yl]-[1-(pyridin-2-ylmethyl)benzimidazol-2-yl]methanone

Participants

Reaction Steps

Combine 1-(3,4,5-trimethoxy-benzoyl)-3-[2-[4-[1 H-benzoimidazole-2-carbonyl]-piperidin-1-yl]-ethyl]-3-(3,4-dichloro-phenyl)-pyrrolidine methanesulfonate salt (0.60 g, 0.70 mmol) and 2-(chloromethyl)pyridine hydrochloride (0.46 g, 2.8 mmol), and potassium carbonate (1.14 g, 8.25 mmol) in acetone (12 mL) and water (4 mL). Heat to reflux. After 24 hours, cool to ambient temperature and concentrate the reaction mixture in vacuo and dilute with ethyl acetate. Extract with water, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution. Dry the organic layer over MgSO4, filter, and concentrate in vacuo to give a residue. Chromatograph the residue on silica gel eluting with 10/1/0.1 dichloromethane/methanol/ammonium hydroxide to give the title compound: Rf=0.58 (silica gel, 10/1/0.1 dichloromethane/methanol/ammonium hydroxide).

Provenance & Evidence